Organic phosphites have long been known as process stabilizers. The exact chemical structure of the phosphite, however, is important in determining the particular efficacy of said phosphite as a process stabilizer.
The compounds and compositions of this invention are structurally distinct from the prior art compounds and compositions of U.S. Pat. Nos. 4,318,845; 4,374,219; 4,524,166; and 2,841,607; and EP 511,156 A2. In addition, the instant compounds and compositions of this invention offer the following advantages over the prior art compounds and compositions:
(1) Superior polymer stabilizing properties during high temperature processing; PA1 (2) Low color development and color maintenance during processing especially when used in combination with phenolic antioxidants; PA1 (3) Superior storage stability particularly hydrolytic stability; PA1 (4) Better compatibility with and ease of incorporation into the substrate to be stabilized; PA1 (5) Superior physical forms which provide advantages in handling, transporting, and blending; and PA1 (6) More effective incorporation in spray on applications resulting in superior in polymer performance. PA1 (1) Novel alkanolamine esters of acyclic phosphites; PA1 (2) Stabilized polyolefin compositions containing novel alkanolamine esters of acyclic phosphites that provide melt flow stabilization and color retention during processing; and PA1 (3) Stabilized polyolefin compositions containing novel alkanolamine esters of acyclic phosphites in combination with a hindered phenolic antioxidant and/or a hindered amine stabilizer and/or a hydroxylamine and/or a benzofuran-2-one. PA1 m is 2, then n is 1 and p is 0; PA1 m is 3, then n is 0 and p is 0; PA1 A is alkylene of 2 to 8 carbon atoms or cycloalkylene of 5 to 6 carbon atoms; PA1 R, R.sub.1, R.sub.2, R.sub.5 and R.sub.6 are independently hydrogen or alkyl of 1 to 18 carbon atoms or phenyl; PA1 R.sub.3 is hydrogen, alkyl of 1 to 18 carbon atoms, phenyl or a group of the formula ##STR2## wherein Y is a group of the formula ##STR3## A' is alkylene of 2 to 8 carbon atoms or cycloalkylene of 5 to 6 carbon atoms, PA1 when m' is 1, then p' is 1, PA1 when m' is 2, then p' is 0, and PA1 q is 0-5 with A, R, R.sub.1, R.sub.2, R.sub.5 and R.sub.6 being as previously defined, with the proviso that, when p and q are 0, then --N--A'--N-- can be a diazacycloalkylene group of 4 to 10 carbon atoms; or PA1 when m is 1 and p is 0, then N--R.sub.3 is an azacycloalkyl group of 4 to 10 carbon atoms or an azaoxacycloalkyl group of 4 to 7 carbon atoms; and PA1 R.sub.4 is hydrogen, alkyl of 1 to 18 carbon atoms or phenyl; and PA1 with the further proviso that when R is tert-butyl, R.sub.1 and R.sub.5 are 4-tert-butyl, and R.sub.2 and R.sub.6 are 6-methyl, then m is 3. PA1 R is iso-propyl, sec-butyl, tert-butyl, tert-amyl or tert-octyl group, PA1 R.sub.1 and R.sub.5 are alkyl of 1 to 8 carbons, and R.sub.1 and R.sub.5 are in the ortho or para position to the phosphite oxygen in each of the phenyl rings; and PA1 m is 3, and n and p are 0. PA1 (a) an organic material subject to thermal, oxidative or actinic induced degradation, and PA1 (b) an effective stabilizing amount of an alkanolamine ester of formula I as defined above. PA1 a) radical polymerisation (normally under high pressure and at elevated temperature). PA1 b) catalytic polymerisation using a catalyst that normally contains one or more than one metal of groups IVb, Vb, VIb or VIII of the Periodic Table. These metals usually have one or more than one ligand, typically oxides, halides, alcoholates, esters, ethers, mines, alkyls, alkenyls and/or aryls that may be either .pi.- or .sigma.-coordinated. These metal complexes may be in the free form or fixed on substrates, typically on activated magnesium chloride, titanium(III) chloride, alumina or silicon oxide. These catalysts may be soluble or insoluble in the polymerisation medium. The catalysts can be used by themselves in the polymerisation or further activators may be used, typically metal alkyls, metal hydrides, metal alkyl halides, metal alkyl oxides or metal alkyloxanes, said metals being elements of groups Ia, IIa and/or IIIa of the Periodic Table. The activators may be modified conveniently with further ester, ether, amine or silyl ether groups. These catalyst systems are usually termed Phillips, Standard Oil Indiana, Ziegler (-Natta), TNZ (DuPont), metallocene or single site catalysts (SSC). PA1 octyl-N-(3,5-di-tert-butyl-4-hydroxyphenyl)-carbamate PA1 R.sub.12 is hydrogen; PA1 R.sub.14 is hydrogen, alkyl having 1 to 12 carbon atoms, cyclopentyl, cyclohexyl or chlorine; PA1 R.sub.13 has the meaning of R.sub.12 or R.sub.14 or is a radical of the formula ##STR5## in which R.sub.16 is hydrogen, alkyl having 1 to 18 carbon atoms, alkyl having 2 to 18 carbon atoms which is interrupted by oxygen or sulfur, dialkylaminoalkyl having a total of 3 to 16 carbon atoms, cyclopentyl, cyclohexyl, phenyl or phenyl which is substituted by 1 to 3 alkyl radicals together having at most 18 carbon atoms; PA1 n is 0, 1 or 2; PA1 the substituents R.sub.17, independently of one another, are hydrogen, alkyl having 1 to 18 carbon atoms, cyclopentyl, cyclohexyl, phenyl, phenyl which is substituted by 1 or 2 alkyl radicals together having at most 16 carbon atoms, a radical of the formula ##STR6## or together with the nitrogen atom to which they are attached form a piperidine or morpholine radical; PA1 m is 1 to 18; PA1 R.sub.20 is hydrogen, alkyl having 1 to 22 carbon atoms or cycloalkyl having 5 to 12 carbon atoms; PA1 A is alkylene having 2 to 22 carbon atoms which may be interrupted by nitrogen, oxygen or sulfur; PA1 R.sub.18 is hydrogen, alkyl having 1 to 18 carbon atoms, cyclopentyl, cyclohexyl, phenyl, phenyl which is substituted by 1 or 2 alkyl radicals together having at most 16 carbon atoms, or is benzyl; PA1 R.sub.19 is alkyl having 1 to 18 carbon atoms; PA1 D is --O--, --S--, --SO--, --SO.sub.2 --or --C(R.sub.21).sub.2 --; PA1 the substituents R.sub.21, independently of one another, are hydrogen, C.sub.1 -C.sub.16 alkyl, the two R.sub.21 together containing 1 to 16 carbon atoms, R.sub.21 is furthermore phenyl or a radical of the formula ##STR7## in which n, R.sub.16 and R.sub.17 are as defined above; E is a radical of the formula ##STR8## in which R.sub.11, R.sub.12 and R.sub.14 are as defined above; and R.sub.15 is hydrogen, alkyl having 1 to 20 carbon atoms, cyclopentyl, cyclohexyl, chlorine or a radical of the formula ##STR9## in which R.sub.16 and R.sub.17 are as defined above, or R.sub.15 together with R.sub.14 forms a tetramethylene radical. PA1 I. Primary, secondary or tertiary aliphatic or cycloaliphatic mines and mine-salts of organic and inorganic acids, e.g. oil-soluble alkyl-ammonium carboxylates PA1 II. Heterocyclic compounds, e.g. substituted imidazolines and oxazolines.